Reacción #1994262

Ecuación de reacción

potassium carbonate

10-(biphenyl-4-yl)-2-bromo-7-phenyl-9,10-dihydroacridine

N-(biphenyl-4-yl)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)biphenyl-4-amine

→

N-(biphenyl-4-yl)-N-(4-(10-(biphenyl-4-yl)-7-phenyl-9,10-dihydroacridin-2-yl)phenyl)biphenyl-4-amine

Rendimiento 65.0%

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.DISTILLATIONThen, distilled water (70 mL)
2. 2
   workup.ADDITIONwas added
3. 3
   Otropurified by silica gel
4. 4
   ExtracciónThen, a toluene layer was extracted
5. 5
   ConcentraciónThe extracted organic solvent was concentrated
6. 6
   Otroremoved
7. 7
   workup.ADDITIONmethanol was added
8. 8
   Otroto produce a solid
9. 9
   FiltraciónThrough filtration
10. 10
    Otroa yellowish brown solid was obtained
11. 11
    OtroIt was purified through silica gel column chromatography (methylene chloride/n-hexane (1/10))

Procedimiento

10-(biphenyl-4-yl)-2-bromo-7-phenyl-9,10-dihydroacridine (14 g, 28.6 mmol) was dissolved in toluene (500 mL) under a nitrogen atmosphere. Then, N-(biphenyl-4-yl)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)biphenyl-4-amine (15 g, 28.6 mmol) was added thereto. To the resultant mixture solution, tetrakis triphenyl phosphine palladium (1.32 g, 1.14 mmol) and potassium carbonate (9.9 g, 71.5 mmol) were added. Then, distilled water (70 mL) was added thereto, followed by reflux-stirring for 4 hours. The resultant solution was cooled to about 60° C., and purified by silica gel. Then, a toluene layer was extracted. The extracted organic solvent was concentrated and removed, and methanol was added to produce a solid. Through filtration, a yellowish brown solid was obtained. It was purified through silica gel column chromatography (methylene chloride/n-hexane (1/10)) to obtain N-(biphenyl-4-yl)-N-(4-(10-(biphenyl-4-yl)-7-phenyl-9,10-dihydroacridin-2-yl)phenyl)biphenyl-4-amine as a Cpd 14 compound (15 g, yield 65%, pale yellow solid).

Fuente